In all seriousness if we're talking about making what would well and truly be the worst map we can make, then we'd be trying to ensure that the player is as miserable as possible for as long as possible. The purest distillation of mapping cruelty, in my opinion, would be this:

 

The player begins with a blue-key door to their back. They're standing on a straight, flat passageway suspended high above a pit of inescapable nukage. You need to get all the way to the other end of a ludicrously long hallway that does not even honor you with a right angle. Along the way, you will need to fight dozens and dozens of barons of hell, equipped only with the pistol, which you are given such an extreme amount of ammo for that you pretty much win for free if you press ADADADAD and have a LOT of time on your hands. This is made all the more unbearable by the fact that the passageway you're walking on has no outer walls to prevent you from falling into the nukage, so if you try to run past the barons, you're playing a dangerous game. (For added infuriation, deliberately put the passageway on top of a blockmap so the pistol doesn't work half the time.)

 

Once you finally get to the end of the hallway, you get the blue key. There is a red door at this end of the hallway, but no red key yet. You have to walk all the way back to open the door at the start. This crosses a linedef, causing the exact same amount of barons as before, plus one more, to teleport in. You have to do the same thing again. Also worth noting is that barons will never teleport in behind you, so literally the only combat skill being tested here is your ability to strafe. Having fun yet?

 

When you finally get back to the blue door, it opens up into an absolute motherfucker of a labyrinth full of specters, which you similarly need to kill with the pistol. The tunnels are narrow, underlit, and completely indistinguishable from each other. There is a secret super shotgun hidden in one of the labyrinth's tunnels, but the map has no ammo for it, so you can only shoot it four times before needing to put it away forever. Also hidden in the tunnels is a hidden linedef disguised as a dead end that, once crossed, silently opens up a door in the other end of the labyrinth, which itself was previously a dead end, but now has the red key in it. Find it, grab it, and leave the labyrinth, only to find out that another fucking avalanche of barons – again, plus one more – has warped in. Walk all the way to the other end of the entire passage for the third time now, open the red key, and walk forward. You get the yellow key, finally, but if you walk a little more forward you enter a tiny hallway with a 90° turn in it that leads you to an exit door locked behind bars. Gonna have to come back here later.

 

Then you walk back out and there's more barons. This time with a single hell knight also thrown into the mix to keep things interesting. You trudge through them, find your way through the labyrinth (which has been refilled with barons instead of specters this time), open the yellow key, and hit a switch.

 

Now, naturally, you begin the trek back to the exit door. More barons. You know the drill by now. After yet another time slumming it through the baron paparazzi, you get to the end of the hallway and turn that 90° corner only to realize that the switch did not actually open the exit door. You've been duped. And now that you've been duped, you come back out and yet ANOTHER glut of barons inundate the map. You fight all the way back to the other end of the hallway and find out that what that switch ACTUALLY opened was a previously-unmarked door in the nukage pit below, and it was literally right outside the labyrinth entrance. Jump down there and go through a teleporter to the final room.

 

The final room is the size of the outdoor area at the end of TNT map 21 except it's all FIREBLU and there's no lighting effects or height differences. It gives the player a megasphere and a BFG and a full 600 cells for it; picking up the goods crosses a linedef that lowers an enormous STARTAN tower in the center. Dramatically. We'll say an entire dramatic sixty seconds of tower-lowering. This reveals a single baron with its back to you, who you then run at and kill in one shot. The capstone to this agonizing baronthon is that you're now trapped in this FIREBLU room and need to search for a tiny, indistinguishable E1M8-style kill sector that you then need to die on, and since you just ate a megasphere, that takes forever. You have now beaten the worst map that could ever possibly be conceived.

 

Also, Hiding the Secrets is the MIDI.